Hudson Valley Cornucopia Bike Tour

Explore the history, culture, and natural beauty on this spectacular Hudson Valley bike tour.

Destination

New York

Activity

Biking

Level

Intermediate

Duration

6 days / 5 nights

From $2,995 PP 6 days / 5 nights

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Settled by Europeans for almost 400 years, the Hudson Valley of New York State served as the backbone of trade and culture in early America. In 1825 the Erie Canal opened from Albany to Buffalo and connected the Hudson River to the Great Lakes, further cementing the river’s status as one of the most important trade routes in the newly founded United States. In the 200 years since, the Hudson Valley has become a center of history, culture, and economic growth for America – all within a half day’s drive for millions of Americans.

If you desire to visit an area that has the best of everything for an enjoyable, accessible, and spectacular cycling tour, this Dutchess and Ulster County tour should be at the top of your list! There are quaint inns in historic villages for lodging and a spectacular selection of restaurants with world-famous chefs, many trained at the nearby Culinary Institute of America. Visit fascinating places like the Franklin Roosevelt Presidential Museum, a spectacular airshow at the Old Rhinebeck Aerodrome, and numerous other historic sights. Enjoy picturesque views as we explore rolling farm hills in Dutchess County, observe the towering peaks of the Catskills from alongside the Ashokan Reservoir, and visit panoramic riverscapes from the stunning Walkway Over the Hudson. This tour delivers the best of everything in this beautiful and culturally rich area…all delivered to you while traveling scenic cycling routes that will thrill riders.

Tour Essence

Experience a fascinating museum and live exhibitions of early aviation pioneers using authentic aircraft at the Old Rhinebeck Aerodrome.
Cycle across the Walkway Over the Hudson as you take in the awesome regional views from this former railroad bridge that towers 200 feet above the river.
Visit the futuristic architectural triumph of the Fisher Center at Bard College, designed by world-renowned architect Frank Gehry.
Sample the selection of craft breweries and wineries that fill the Hudson Valley countryside.
Visit the site of prohibition gangster Dutch Schutlz’s secret bootlegging operation – and sample the spirits brewed there (legally) today!
Tour the Franklin Roosevelt Presidential Home and Museum in Hyde Park.
Visit aristocratic mansions from the Gilded Age like those of the Vanderbilt and Mills families.
Explore the fascinating villages of Tivoli, Rhinebeck, New Paltz, Rosendale, High Falls, and Kingston.
Cycle along the shore of Ashokan Reservoir with its spectacular views of Catskill peaks.
Enjoy lunch at the Culinary Institute of America, one of the world’s leading schools for chefs
Ride on the constantly expanding network of New York State rail trails, including sections of the 750-mile Empire State Trail.
Sightsee as you ride through the historic Huguenot District in New Paltz.

What to Expect

Start Location

Rhinebeck, NY

End Location

Rhinebeck, NY

Mileage

Average Daily: 38 Total: 225

Elevation

Average Daily: 2,067 feet Total: 12,400 feet

Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.

Van Support
The services of 2 bike tour guides
Abundant Snacks
Ciclismo Classico Jersey
Cultural visits and tours
Alcoholic beverages are not included

Bring your own! Bikes are not included for this specific trip.

Call us if you need a rental bike!

All accommodations
All 2 breakfasts
4 lunches
3 dinners

Visit to Old Rhinebeck Aerodrome museum and air show (weather permitting)
Visit to former Dutch Schultz bootleg distillery site
Lunch at Culinary Institute of America
Visit to Fisher Arts Center at Bard College
Visit to Roosevelt Museum and Home
Ride Across Walkway Over the Hudson
Visit to Vanderbilt Mansion
Lunch in historic Rondout District of Kingston
Visit to historic Huguenot District in New Paltz
Lodging in historic Rosendale

Itinerary

Start Location

Rhinebeck, NY

Fly Into

Newburgh (SWF) Airport

End Location

Rhinebeck, NY

Fly Out Of

Newburgh (SWF) Airport

Download Itinerary

STYLED MAP

Day1

The Birth of Flight at Old Rhinebeck Aerodrome

Our first day’s ride takes us into the gently rolling countryside of Dutchess County to our highlight stop on today’s tour: the Old Rhinebeck Aerodrome. Founded in 1958, the Aerodrome has developed into America’s premiere flying museum of antique aviation with over 60 vintage aircraft, many of which are in flying condition and are used regularly in the facility’s air shows. Also included are many antique automobiles, motorcycles, and related memorabilia, all displayed in a classic small-town airport setting. You can visit the Aerodrome’s extensive museum in the History of Flight Building, with a comprehensive exhibit of the aircraft, vehicles, engines, and memorabilia that make up the static displays and compose a tribute to the glory of man’s conquest of the air. You will also witness (weather permitting) the Aerodrome’s spectacular live air show with real pioneer aircraft–many are not replicas! It’s the “History of Flight” program that highlights the pioneer era before WWI and the Golden Age of Aviation in the ’20s and ’30s. The Aerodrome will also be our lunch stop on today’s ride, so relax and take your time to enjoy this totally unique attraction. As the saying goes, “It’s the only way to fly!” Today’s ride will also pass through the scenic campus of Bard College with a stop at the eye-popping Fisher Art Center with its gleaming roof of stainless-steel shingles and curved steel, designed by world-famous architect Frank Gehry.

Meals Provided

Lunch, Dinner

Average Mileage

29 miles

Elevation Gain

1350 ft

Riding Terrain

Meals Provided

Lunch, Dinner

Accommodations

Beekman Arms Hotel and Delameter Inn

Since before the Revolutionary War, Rhinebeck’s Beekman Arms has welcomed guests since 1766 to the beauty of the Hudson Valley. The Delamater property includes both historic and modern buildings to guests seeking a comfortable and unique stay in historic Dutchess County, NY. The hotel is in the center of the equally historic village of Rhinebeck with shopping and restaurants all within a short walk.

Luxury Level3 star

Day2

Bootlegger’s Hideout

Our second day of riding will see us once again exploring the rolling countryside east of the Hudson. This rural area supplies space for horse and crop farming, and during the Prohibition Era early in the 20th century its hills and hollows provided ideal cover for huge, gangster-run bootlegging operations. When federal agents raided a local farm in Pine Plains in the fall of 1932, they uncovered a massive underground concrete bunker containing two 2,000-gallon stills, 10,000 pounds of sugar, and 1,000 gallons of Sugar Wash Moonshine. A sprawling network of interconnected tunnels spread throughout the property to facilitate the production and shipping of illegal “hooch.” Legend has it that the notorious New York City bootlegger Dutch Schultz was the mastermind and financier of the operation. Today the site has been redeveloped by locals into a legal distilling site where the first new batches were made in 2020 after an 88-year break. After our main stop here, we will casually ride our way back to our hotel to relax and trade stories about all the scenery we’ve seen and the memories we’ve created today.

Meals Provided

Lunch, Dinner

Average Mileage

44 miles

Elevation Gain

2,800 feet

Meals Provided

Lunch, Dinner

Accommodations

Beekman Arms Hotel and Delameter Inn

Luxury Level3 star

Day3

Roosevelt Ramble

Today our ride destination is the Franklin Roosevelt Presidential Museum and Home in Hyde Park. Roosevelt was the 32nd President of the United States, architect of the New Deal, and Commander-in-Chief during World War II. He is arguably one of the most influential figures in the history of the United States, and the American society we live in today is heavily influenced by his vision; Social Security, the minimum wage, a 40-hour workweek, child labor laws, the World Bank, NATO, and the United Nations are all just a small part of the Roosevelt legacy. His wife, Eleanor Roosevelt, was also a major historical influence as the first Chair of the United Nations Human Rights Commission, a prolific writer, and an outspoken advocate for democracy, civil rights, and social justice. To reach the home and library, we will pedal south along the Hudson, catching occasional glimpses of its water as we navigate the hills and hollows via bucolic roads that traverse a rural countryside dotted with farms and small hamlets.

Average Mileage

34 miles

Elevation Gain

1,700 ft

Accommodations

Beekman Arms Hotel and Delameter Inn

Luxury Level3 star

Day4

Westward! Across the Hudson

Today’s ride will supply some impressive additions of scenic and historic sites to add your tour memories! We will once again head south along the Hudson, but this time along a different route that will see us visit numerous places steeped in history: Staatsburg State Historic Site, the Mills Mansion, Bard Rock on the Hudson, and the Vanderbilt mansion. Lunch at the Culinary Institute of America will precede our centerpiece attraction: the 1.28 mile long, 200-foot-tall Walkway Over the Hudson. Originally built as a railway bridge in 1889, this incredible structure was opened in 2009 as an integral part of the region’s rail trail network and is a stunning tourist attraction all by itself. You have to see the views to believe them! Once across the bridge, we will follow the Hudson Valley Rail Trail to the eclectic village of New Paltz. After quick rides through New Paltz’s hippie-vibe downtown and Huguenot District, we will head north on the newly renovated (and flat!) Wallkill Rail Trail. A journey over the impressive Rosendale Trestle will take us to our next lodging: the 1850 House Hotel & Tavern (which can be found directly under the trestle). You are going to have a lot to talk about at dinner tonight!

Meals Provided

Lunch

Average Mileage

44 miles

Elevation Gain

1,900 ft

Meals Provided

Lunch

Accommodations

The 1850 House Inn & Tavern

History Is Revived at the 1850 House Inn & Tavern. A new era dawns for Rosendale’s most celebrated historic landmark as a legendary Ulster County hotel and beloved community icon is once again open to guests for the first time in decades. The inn features a comfortable mixture of vintage decor and modern furnishings plus the welcoming 1850 House Tavern. Your hotel is situated in the center of Rosendale, within walking distance to all the attractions of this historic village founded in 1680.

Luxury Level2-Star

Day5

Ashokan Splendor

Our ride today trades the cultural richness of the valley for the scenic splendor of the Catskills as we pedal up into the foothills and past the hamlets of High Falls, Stone Ridge, and Krumville to see stunning views of mountains that have witnessed so much early American history. Eventually, we reach the Ashokan valley, now filled with the Ashokan Reservoir that was constructed in 1915 on the Esopus Creek to supply water to the growing metropolis of New York City. Once you have looked across its waters to the mountain skyline, you will understand how this area became the inspiration for the hauntingly beautiful melody of Jay Ungar’s “Ashokan Farewell.” Then as we head back downhill we will pass the canyon of Esopus Creek below the spillway and continue back down through Marbletown and Cottekill to return to our starting point in Rosendale, where we will also pay tribute to the 19th century’s Widow Jane Mine. Limestone mining in this area provided over half of the cement manufactured in America at its peak in 1891. In the years since the mine has been used for everything from a fallout shelter to mushroom farming, and today is open to visitors and events.

Meals Provided

Breakfast, Lunch, Dinner

Average Mileage

Elevation Gain

3,300

Meals Provided

Breakfast, Lunch, Dinner

Accommodations

The 1850 House Inn & Tavern

Luxury Level2-Star

Day6

Return to The Dutchess

Today may be our last day of pedaling, but there’s still plenty of beauty and fun in store as we first head north along the O&W Rail Trail to see local artist Kat O’Sullivan’s whimsical home next to the trail. The artist owner and her husband took this 170-year-old home and have turned it into a giant art exhibit. You will be amazed! We then rejoin the Wallkill Valley Rail Trail to head north again into the city of Kingston, New York State’s capital from 1777-1797. We will stop for lunch in the city’s waterfront Rondout district, which was a village and important Hudson River shipping and cement manufacturing hub before it merged with Kingston in 1872. Today the neighborhood hosts a waterfront park and a variety of shops and restaurants where you will have time to choose your own leisurely lunch spot. Then we will head north along the Kingston Point and Empire State rail trails while enjoying expansive views of the river as we cross the Kingston-Rhinecliff Bridge to return to our tour starting point in Rhinebeck.

Meals Provided

Breakfast

Meals Provided

Breakfast

Accommodations

Hudson Valley Cornucopia Bike Tour

Luxury Level

Meet Our Guides

John Gillvan

Dave Kraus

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Hudson Valley Cornucopia Bike Tour

Destination

Activity

Level

Duration

Tour Essence

What to Expect

Start Location

End Location

Mileage

Elevation

What's Included

Itinerary

Start Location

Fly Into

End Location

Fly Out Of

The Birth of Flight at Old Rhinebeck Aerodrome

Meals Provided

Average Mileage

Elevation Gain

Riding Terrain

Meals Provided

Accommodations

Beekman Arms Hotel and Delameter Inn

Bootlegger’s Hideout

Meals Provided

Average Mileage

Elevation Gain

Meals Provided

Accommodations

Beekman Arms Hotel and Delameter Inn

Roosevelt Ramble

Average Mileage

Elevation Gain

Accommodations

Beekman Arms Hotel and Delameter Inn

Westward! Across the Hudson

Meals Provided

Average Mileage

Elevation Gain

Meals Provided

Accommodations

The 1850 House Inn & Tavern

Ashokan Splendor

Meals Provided

Average Mileage

Elevation Gain

Meals Provided

Accommodations

The 1850 House Inn & Tavern

Return to The Dutchess

Meals Provided

Meals Provided

Accommodations

Hudson Valley Cornucopia Bike Tour

Meet Our Guides

John Gillvan

Dave Kraus

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